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The Boss Society Podcast
Megan Gillespie
34 episodes
5 days ago
The Boss Society Podcast is where high-achieving women come together to share real business stories, raw conversations, and powerful insights. This isn't just another business podcast—it’s a seat at the table with local women leaders who are making an impact.

Each episode gives you a peek inside the rooms where real business happens, featuring unfiltered advice, behind-the-scenes moments, and conversations that go beyond surface-level success. Whether you’re a seasoned entrepreneur or just getting started, this show will challenge, inspire, and connect you with a community of ambitious women rewriting the rules of business.

Pull up a chair—your voice belongs in this conversation.
Show more...
Entrepreneurship
Business,
Marketing
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All content for The Boss Society Podcast is the property of Megan Gillespie and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
The Boss Society Podcast is where high-achieving women come together to share real business stories, raw conversations, and powerful insights. This isn't just another business podcast—it’s a seat at the table with local women leaders who are making an impact.

Each episode gives you a peek inside the rooms where real business happens, featuring unfiltered advice, behind-the-scenes moments, and conversations that go beyond surface-level success. Whether you’re a seasoned entrepreneur or just getting started, this show will challenge, inspire, and connect you with a community of ambitious women rewriting the rules of business.

Pull up a chair—your voice belongs in this conversation.
Show more...
Entrepreneurship
Business,
Marketing
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Midlife Clarity: Burnout, Boundaries, and Becoming Yourself Again
The Boss Society Podcast
1 hour 9 minutes 55 seconds
2 months ago
Midlife Clarity: Burnout, Boundaries, and Becoming Yourself Again

In this week’s episode of The Boss Society Podcast, Megan sits down with West Olympia real estate guide and community connector Heather Foster for an honest, funny, and deeply relatable conversation about what it means to reinvent yourself — again and again — until it finally feels right.

From raising three kids as a military spouse to moving 20+ times and walking away from her career when it no longer aligned, Heather’s story is a powerful reminder that midlife isn’t a decline... it’s a chance to rise. Together, they unpack what it looks like to rediscover your identity after motherhood, shed people-pleasing, build a business on your own terms, and why collaboration and community are essential for sustainable success.

Whether you're in real estate or not, this episode is full of grounded wisdom for any woman navigating a new season, especially if you're craving space to show up as your truest self.


Key Points:

  • Why reinvention is often just rediscovery
  • What 20+ moves taught Heather about letting go and starting fresh
  • The power of walking away from a business that no longer aligns
  • Midlife as a season of expansion, not invisibility
  • How to stop performing and start leading with truth
  • Why surrounding yourself with the right people changes everything
  • Redefining success outside of hustle culture and industry standards


Special Offer:

If you’re local to the Olympia area and want a real estate guide who sees the whole person, follow Heather at @heathertinolympia or reach out at HeatherFoster@bhhsnw.com. Whether you’re buying, selling, downsizing, starting fresh, or need some recommendations around town... she’s in your corner.


PS: Heather is also joining us at Her Season 🍂✨ a cozy, in-person fall retreat for women entrepreneurs who are ready to reset, reconnect, and rise into what’s next. It’s happening this October on the water in Hood Canal, and you can learn more and apply to join us HERE


Links Mentioned:

  • Follow Heather on Instagram
  • Connect on Facebook
  • Apply for the Her Season Retreat
  • Local shoutouts: Stef McDonald, Olympia Dust Market, Lovely & Dapper Bakery


Chapters:

00:00 Introduction and Personal Journey

06:18 The Impact of Frequent Moves

16:03 Reinvention and Rediscovery

25:13 Navigating Identity Beyond Labels

32:36 Embracing Failure as a Learning Tool

34:07 Navigating the Chaos of the Real Estate Market

36:18 Personal Accountability and Ethical Business Practices

38:24 The Importance of Integrity in Business

41:07 Setting Boundaries for Sustainable Success

44:22 The Power of Collaboration and Delegation

49:41 Finding the Right Mentor and Support System

54:27 Building a Supportive Community

58:29 Taking Charge of Your Business Journey


✨ Leave a Review:

Loving the show? Don’t forget to follow, leave a review, and share this episode with a friend who’s in the middle of their own reinvention.

Loved this episode? Make sure to subscribe so you never miss a conversation inside The Boss Society Podcast! If you found value in today’s episode, share it with a friend or leave a review—it helps more women like you find the show.

✨ Stay connected:

📲 Follow me on Instagram: @themegangillespie @olympiabosssociety

📩 Join the community: www.olympiabosssociety.com

🎙️ Want to be a guest? Apply HERE

Your voice matters. Your seat at the table is waiting. See you next time!

The Boss Society Podcast
The Boss Society Podcast is where high-achieving women come together to share real business stories, raw conversations, and powerful insights. This isn't just another business podcast—it’s a seat at the table with local women leaders who are making an impact.

Each episode gives you a peek inside the rooms where real business happens, featuring unfiltered advice, behind-the-scenes moments, and conversations that go beyond surface-level success. Whether you’re a seasoned entrepreneur or just getting started, this show will challenge, inspire, and connect you with a community of ambitious women rewriting the rules of business.

Pull up a chair—your voice belongs in this conversation.